HCID 86706384, compound → HCID 66546695, compound

HRID 1396951Notes

Reaction equation

HRID 1396951 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C@H:11]2[N:15]([C:16](=[O:35])[C@@H:17]([CH2:23][N:24]([CH:33]=[O:34])[O:25]CC3C=CC=CC=3)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:14]=[CH:13][CH2:12]2)=[O:10])=[N:6][CH:7]=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C@H:11]2[N:15]([C:16](=[O:35])[C@@H:17]([CH2:23][N:24]([CH:33]=[O:34])[OH:25])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:14]=[CH:13][CH2:12]2)=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 86706384HCID 86706384, compound

Product 1

HCID 66546695HCID 66546695, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (5S)—N-(5-fluoro-2-pyridinyl)-1-[(2R)-2-({formyl[(phenylmethyl)oxy]amino}methyl)heptanoyl]-4,5-dihydro-1H-pyrazole-5-carboxamide (180 mg, 0.37 mmol) in methanol (15 mL) was added Pd(OH)2/C (105 mg, 20%, 44% wt). The mixture was stirred under a H2 atmosphere for 30 min and the catalyst was filtered off. The filtrate was concentrated and the residue was purified by HPLC to provide the titled compound (70 mg, 48%) as a white solid. LCMS: (M+H)+: 394.2.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-1568d7fb9f8a4ed0b66fa5595105bb68
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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